LM - Agree with Big C............that would not be the boat I would want for that jaunt = Small & light. But let's not dwell on that.
You will definitely have to check the weather especially wind/wave forecasts.
Caribwx & NOAA will be avail on the web (internet cafes or bars along the way).........a SSB receiver would be great but won't be on the charter boat (portable?). VHF weather will be mixed depending on your language capability.
If you have clear legs & a decision tree for go vs no go (rather than locked to a schedule) at every stop, it will be safer & avoid late nights + missed flight home.
Out of your mind = No......not for salty sailors...........but it would not take much of a stretch to make this a bouncy/wet adventure.
Don't bet the ranch that the wind will be steady out of the east or that your boat will avg 8 kts ie; if you are close hauled reefed in 20kts+ in 6' seas that boat will not do 8kts.
A good handheld GPS for the cockpit would also be a good tool
Then again, the stars could align & you would have a long smooth voyage> will look forward to trip report.